[1] The rhyme was first recorded in print by James Orchard Halliwell in 1842:[2] It gained popularity in the early twentieth century.

[3] One legend suggests[4] that this nursery rhyme originated in the once prosperous wool merchant's village of Lavenham, about 70 miles northeast of London, having been inspired by its multicolored half-timbered houses leaning at irregular angles as if they are supporting each other.

[5] Other sources[6] state that the poem originates from British history, specifically the period of the Scottish Stuart King Charles I of England (reigned 1625–1649).

The crooked man is reputed to be the Scottish General Sir Alexander Leslie, who signed a covenant securing religious and political freedom for Scotland.

[7][8] The great recoinage around 1696 led to sixpence coins that were made of very thin silver and were easily bent, becoming "crooked".